An optically active 1-amino-2-vinylcyclopropanecarboxylic acid ester is, for example, useful as an intermediate for synthesis of medicines such as an antiviral agent.
It is known that an optically active 1-amino-2-vinylcyclopropanecarboxylic acid ester is produced, for example, by reacting an N-phenylmethyleneglycine ester with (E)-1,4-dibromo-2-butene in toluene in the presence of lithium t-butoxide to obtain a 1-N-(phenylmethylene)amino-2-vinylcyclopropanecarboxylic acid ester, subjecting the obtained ester to an acid treatment to synthesize a racemic 1-amino-2-vinylcyclopropanecarboxylic acid ester, protecting an amino group of the thus synthesized 1-amino-2-vinylcyclopropanecarboxylic acid ester with a t-butoxycarbonyl group, performing an optical resolution of the ester by an enzyme reaction to remove the t-butoxycarbonyl group (see, for example, Journal of Organic Chemistry, Vol. 70, pp. 5869-5879, 2005).
However, the above-mentioned method had a problem that it is difficult to reuse an unnecessary isomer through racemization, obtained by the optical resolution of the enzyme reaction, since the 1-amino-2-vinylcyclopropanecarboxylic acid ester has two asymmetric centers.
Under these circumstances, there has been required a novel method for producing the optically active 1-amino-2-vinylcyclopropanecarboxylic acid ester.